In June of 2006, I opened a position that would double in three months.

No, I wasn't investing in wild penny stocks. There were no (ahem) "emerging economies" or sophisticated trading platforms involved, and there were no shady stock promoters to pay off before I could collect my profits. My secret? LEAPs, an acronym for long-term equity anticipation securities.

Or, in simpler terms: long-term call options.

Why your portfolio should take a LEAP of faith
I'll have more in a minute on how LEAPS led to a 120% gain in a quarter. First, let's talk about what LEAPs are. They're options that combine an intrinsic value with a time value. Motley Fool Options co-advisor Jim Gillies does an excellent job of explaining this concept in detail; please read it if you're thinking of trying options as an investment alternative.

What makes LEAPs more interesting than your average call option is their above-average time value. Instead of expiring in a month or a quarter, LEAPs give the patient investor more than a year to wait for catalysts to unlock value.

"Two and a half years is often enough time for many just plain cheap stocks either to be discovered or to regain popularity," writes Joel Greenblatt in You Can Be a Stock Market Genius.

Fortunately, I didn't need two and a half years. Three months was more than sufficient.

Steve Jobs made me rich
Interestingly, I wasn't buying a super-cheap stock. Apple (Nasdaq: AAPL) traded at a hefty multiple to earnings in June of 2006, more than I wanted to pay. But I loved the business. Also, at roughly $56 a stub, I suspected that a brutal summer downturn had led Wall Street to sharply underestimate the long-term implications of Apple's budding partnership with Intel (Nasdaq: INTC).

What I needed was a way to compensate for the risks involved with holding a stock that boasted a premium valuation. LEAPs offered the answer. For $8 per share in the contract, I purchased LEAPs with a strike price of $70.

If that seems crazy, it sort of was. The intrinsic value of the option was zero. To break even, the stock would have to be trading for at least $78 at the time of expiration -- the $70 stock price plus my $8-per-share time-value premium. I was counting on having shares of Apple rise by at least 40% in 18 months -- not exactly a sure thing.

So why did I do it? I set the odds at 50-50 that Apple could gain at least a point of market share from PC peers by selling Windows-compatible Macs. I also suspected that, if I was right, the market would reward Apple by pushing its shares close to $100 apiece, at which point I'd own a LEAP worth at least $30 in intrinsic value, a near four-bagger. The math favored my bet. (A minimum 3.75-to-1 return versus a 1-in-2 chance of a complete loss.)

Gaming investors might recognize this math. Las Vegas Sands (NYSE: LVS), Melco Crown Entertainment, and their peers profit by exploiting the mathematical edges built into their casino games. It's usually enough to service billions in construction debt. My edge was less certain, but I liked my chances to profit.

When I sold the LEAPs at $17.72 apiece -- more than double my purchase price of $8 -- on Oct. 16, 2006, shares of Apple closed at $75.40, above my strike price yet with plenty of time value still remaining. I sold because a scandal over employee stock-options pricing was obscuring the risks involved with holding a leveraged position in Apple.

Eric Schm ... I mean, I made myself poor
For as many stories like this one, there are more stories of investors who lose big with LEAPs and options in general. I lost big on 2010 LEAPs in Google (Nasdaq: GOOG).

I bought in July of 2008 at a strike price of $450 a share -- well below what the stock was trading for at the time -- but without first identifying any short-term catalysts that would lead the shares higher. I sold in November 2009, realizing a 30% loss.

In hindsight, I shouldn't be surprised. Catalysts often precede returns. Sirius XM Radio (Nasdaq: SIRI) has rebounded nicely since stabilizing its balance sheet. A 2.0 version of the service, built in part on the Android OS, could help further juice returns.

Qlik Technologies (Nasdaq: QLIK) has rallied impressively on the strength of mainstream adoption of business-intelligence technology that for years had remained trapped in the executive suite. More than 19,000 now use its QlikView software, up from 14,000 a year ago.

Catalysts matter, and I've done well when I've paid attention to them. For example, when I deduced that the real value of Marvel's studio business would become clear to the Street after the release of 2008's Iron Man, I bought LEAPs to accompany my core position in the shares. Each purchase was a winner.

A final few words of Foolish advice
LEAPs are for neither the faint of heart nor the inattentive. It takes serious study to identify and then handicap catalysts. Yet I've been a net winner with these tools, and Greenblatt -- a master value investor if ever there was one -- endorses them for special situations.

Plus, there will always be opportunities to profit with LEAPs. Apple looks like it's giving investors yet another interesting opportunity. The Mac maker has a history of blowing away analyst projections yet continues to be valued below the Street's long-term consensus profit estimate. My own math puts Apple at $600 a share within three years. Why not take a look at the LEAPs? January 2013 calls with a $400 strike price trade for just $27 a share as of this writing. If I'm right and the stock rises to, say, $500 by that time, today's investors would be sitting on a three-bagger.

Of course, there are many options when it comes to options, including several lower-risk strategies worth employing. Care to learn more? Enter your email address in the box below to find out about our Motley Fool Options service.

The original version of this article first appeared on Aug. 17, 2009. It has been updated.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.